Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H20N4O2.2ClH.H2O |
Molecular Weight | 415.314 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.Cl.CN(C)CCCNC1=C2C=CC=CC2=NC3=C1C(=CC=C3)[N+]([O-])=O
InChI
InChIKey=NHZMLGQMVDPHND-UHFFFAOYSA-N
InChI=1S/C18H20N4O2.2ClH.H2O/c1-21(2)12-6-11-19-18-13-7-3-4-8-14(13)20-15-9-5-10-16(17(15)18)22(23)24;;;/h3-5,7-10H,6,11-12H2,1-2H3,(H,19,20);2*1H;1H2
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H20N4O2 |
Molecular Weight | 324.377 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Nitracrine (Ledakrin, C-283) is an acridine derivative with potential cytostatic and antitumor activities. Nitracrine induces the unwinding of supercoiled DNA and binds to the DNA through intercalation, forming drug-DNA adducts and DNA interstrand crosslinks. This inhibits RNA synthesis, protein production, cell growth, DNA replication and cell proliferation; altogether, this may promote apoptosis. Since cancer cells have increased metabolism and proliferate at an increased rate, nitracrine may induce tumor cell apoptosis. The drug was used in clinics in Poland for the treatment of ovarian, colon, lung and mammary carcinomas. Some undesirable effects observed in clinics: e.g. nausea, vomiting and toxicity and mutagenicity of the
drug in S. typhimurium strongly limited the therapeutic use of nitracrine and promoted a search for more suitable analogues.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7789719
Curator's Comment: The lack of bone marrow toxicity and the
poor penetration of the central nervous system by nitracrine are attractive features of the drug.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7789719
Curator's Comment: Nitracrine belongs to a
group of several hundred acridine derivatives synthesized by the group formerly led in Gdansk
(Poland) by Zygmunt Ledochowski and then by
Andrzej Ledoehowski.
Approval Year
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6696822
Nitracrine displayed slective toxicity towards hypoxic AA8 cells, with a pronounced differential between killing of aerobic and hypoxic cells at a concentration of 0.1 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:11:04 GMT 2023
by
admin
on
Sat Dec 16 11:11:04 GMT 2023
|
Record UNII |
7G5S4303OI
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
55429-45-3
Created by
admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
|
PRIMARY | |||
|
7G5S4303OI
Created by
admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
|
PRIMARY | |||
|
m7927
Created by
admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
|
PRIMARY | Merck Index | ||
|
72941568
Created by
admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ANHYDROUS->SOLVATE |